Adding a tee to my pitless

Im going to be winterizing my cottage (in Canada) for the first time and was wondering if there was any issue with adding a tee with a valve to the drop side of the pitless adaptor ? That way next fall I just have to crack the valve and I can drain all the water out of the line instead of having to pull the pitless up and down every year. I know Ill still have to fish a tool down to open and close the valve but this seems like less of a hassle to me (or even better I could build a nice lever handle and extend it up...).

So the bleeder is essentially a reverse check valve with a low cracking pressure ? Will it bleed out during usage causing my pump to cycle constantly ? Or does it only open up once my pump is powered down and ive depressurized the lines ?

Whats the reliability of these things ? Im an engineer and I have check valves fail regularly on gas streams in my systems regularly

What about if I want to blow the lines out with compressed air ? Will the bleeder not close ?

A bleeder will work fine for a winter bleed back using a bladder style tank as well. Just don’t use a check valve after the bleeder, then it will always have pressure on it when the pump is energized, and it won’t open.

When you need to winterize, just turn off power to the pump, and open the faucets in the house. When all the pressure is out of the system, the bleeder will automatically open and drain the lines down as needed.